Antibacterial and antifungal composition

ABSTRACT

An antibacterial and antifungal composition comprising (A) at least one member selected from the group consisting of dehydroacetic acid, sorbic acid and their alkali metal salts and (B) at least one member selected from the group consisting of o-phenylphenol and its alkali metal salts, p-chloro-m-xylenol, 2-(4-thiazolyl)-1H-benzimidazole, 8-hydroxyquinoline and its salts and chelates, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, tetrachloroisophthalonitrile and N-(fluorodichloromethylthio)phthalimide. The antibacterial and antifungal effects can be synergistically increased when the component (A) is employed in combination with the component (B).

This is a division of application Ser. No. 58,448, filed July 8, 1979, now U.S. Pat. No. 4,242,356 issued Dec. 30, 1980.

BACKGROUND OF THE INVENTION

The present invention relates to a composition useful as antibacterial and antifungal agent, and more particularly to a composition mainly containing dehydroacetic acid, sorbic acid or their alkali metal salts.

It is well known that dehydroacetic acid, sorbic acid and their alkali metal salts are useful as antibacterial and antifungal agents. The toxicity of these antibacterial and antifungal agents is so low that their addition to foods is permitted, and they are agents of very high safety. Therefore, if these agents are usable in any fields such as general industrial products and agricultural products, to say nothing of foods, the usefulness of these agents becomes very great. However, the antibacterial and antifungal effects thereof are not always satisfactory, and they are restricted in the application to industrial products such as paints, sizing agents and adhesives.

SUMMARY OF THE INVENTION

In accordance with the present invention, there is provided an antibacterial and antifungal composition comprising (A) at least one member selected from the group consisting of dehydroacetic acid, sorbic acid and their alkali metal salts and (B) at least one member selected from the group consisting of o-phenylphenol and its alkali metal salts, p-chloro-m-xylenol, 2-(4-thiazolyl)-1H-benzimidazole, 8-hydroxyquinoline and its salts and chelates, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, tetrachloroisophthalonitrile and N-(fluorodichloromethylthio)phthalimide. The synergistic effect on the antibacterial and antifungal properties is very remarkable, when the component (A) is employed in combination with the component (B), and the composition of the invention can be availably employed as antibacterial and antifungal agents in various industrial products and agricultural products.

DETAILED DESCRIPTION

There are employed, as the component (A) of the composition of the invention, dehydroacetic acid, sorbic acid and their alkali metal salts such as sodium dehydroacetate, potassium dehydroacetate, sodium sorbate and potassium sorbate. These compounds may be employed alone or in admixture thereof.

Examples of a compound employed as the component (B) of the composition of the invention are o-phenylphenol and its alkali metal salts shown by the following formula: ##STR1## wherein X is hydrogen or an alkali metal, p-chloro-m-xylenol shown by the following formula: ##STR2## 2-(4-thiazolyl)-1H-benzimidazole shown by the following formula: ##STR3## 8-hydroxyquinoline shown by the following formula: ##STR4## salts of 8-hydroxyquinoline with organic or inorganic acids such as hydrochloric acid, sulfuric acid and acetic acid, e.g. 8-hydroxyquinoline sulfate of the formula: ##STR5## chelates of 8-hydroxyquinoline with metals such as copper and zinc, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate shown by the following formula: ##STR6## tetrachloroisophthalonitrile shown by the following formula: ##STR7## and N-(fluorodichloromethylthio)phthalimide shown by the following formula: ##STR8## These compounds may be employed anone or in admixture thereof.

The components (A) and (B) may be employed in any proportions. In general, it is desirable to employ the component (B) in an amount of 1% to 40% by weight based on the total weight of the composition, since the particularly remarkable synergistic effect can be obtained. As stated before, the feature of the present invention is that the antibacterial and antifungal effects of dehydroacetic acid, sorbic acid or their alkali metal salts can be remarkably increased by the combination use with a slight amount of the component (B). Although the compounds employed as the component (B) are known as antibacterial and antifungal agents, it has now been found that synergistic antibacterial and antifungal effect unexpected from a single use of various known antibacterial and antifungal agents can be obtained, when among known antibacterial and antifungal agents the component (A) and the component (B) are particularly combined. When the content of the component (B) is less than 1% by weight, sufficient synergistic effect cannot be obtained. Also, even if the component (B) is employed in an amount of more than 40% by weight, the synergitic effect is not increased. Further, the compounds employed as the component (B) are relatively expensive and also the toxicity is higher than the component (A) and, therefore, the use of the component (B) in an amount of more than 40% by weight not only be uneconomical, but also may impair the low toxicity which is the feature of the composition of the present invention.

The adding amount of the composition varies depending on the kind of the products to be added. In general, sufficient antibacterial and antifungal effects can be obtained in an amount of 50 to 8,000 p.p.m.

Auxiliary agents such as other bactericides, other fungicides, surface active agents and perfumes may be incorporated in the composition of the invention, as occasion demands.

The composition of the present invention is applicable to any industrial products and agricultural products which require the annihilation or the prevention of propagation of bacteria and fungi, such as paints, sizing agents, petroleum products, plastic moldings, fibers, leathers, woods, paper goods, cosmetics, pharmacuticals, medical appliances, industrial equipments and building materials (putties, fiber boards, particle boards, gypsum boards), fruits, grains and vegetables.

The present invention is more particularly described and explained by means of the following Examples, in which all % are by weight unless otherwise noted.

EXAMPLE 1

A liquid culture medium of pH 7.0 containing 1% of peptone, 1% of meat extract and 0.1% of sodium chloride was prepared and sterilized, and 10 ml. portions thereof were poured into L-shaped tubes. After adding a prescribed amount of an antibacterial, antifungal composition consisting of the components (A) and (B) as shown in Table 1 to each tube, 0.1 ml. (number of cells: 5×10⁴ cells/ml.) of an aqueous suspension of bacteria as shown in Table 1 was added to each tube. The thus prepared culture liquor contained 5×10² cells per milliliter. The culture was carried out at 37° C. for 48 hours with reciprocal shaking, and the state of the growth of bacteria was then observed by measuring the number of cells in 1 ml. of the culture liquor.

The results are shown in Table 1.

                                      TABLE 1                                      __________________________________________________________________________                                              Amount of                             Antibacterial, antifungal composition    composition                                                                           Number of                                                         (A)/(B)                                                                              added  cells                          Bacteria                                                                               Component (A)                                                                               Component (B) by weight                                                                            (p.p.m.)                                                                              (cells/ml.)                    __________________________________________________________________________     Staphylococ-                                                                           Sodium dehydroacetate                                                                       N-(fluorodichloro-                                        cus aureus           methylthio)phthalimide                                                                       95/5  500    25 × 10                                                     95/5  1000   3 × 10                                                      90/10 500    18 × 10                                                     90/10 1000   0                                                                 80/20 500    17 × 10                                                     80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    19 × 10.sup.5                                               100/0 1000   18 × 10.sup.3                                               0/100 25     11 × 10.sup.8                                               0/100 50     10 × 10.sup.5                                               0/100 100    7 × 10.sup.4                                                0/100 200    6 × 10.sup.2             Staphylococ-                                                                           Potassium sorbate                                                                           N-(fluorodichloro-                                        cus aureus           methylthio)phthalimide                                                                       95/5  500    30 × 10                                                     95/5  1000   6                                                                 90/10 500    22 × 10                                                     90/10 1000   0                                                                 80/20 500    14 × 10                                                     80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    25 × 10.sup.7                                               100/0 1000   9 × 10.sup.5                                                0/100 25     11 × 10.sup.8                                               0/100 50     10 × 10.sup.5                                               0/100 100    7 × 10.sup.4                                                0/100 200    6 × 10.sup.2             Staphylococ-                                                                           Sorbic acid  N-(fluorodichloro-                                        cus aureus           methylthio)phthalimide                                                                       95/5  500    25 × 10                                                     95/5  1000   0                                                                 90/10 500    15 × 10                                                     90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    21 × 10.sup.6                                               100/0 1000   5 × 10.sup.3                                                0/100 25     11 × 10.sup.8                                               0/100 50     10 × 10.sup.5                                               0/100 100    7 × 10.sup.4                                                0/100 200    6 × 10.sup.2             Bacillus                                                                               Sodium dehydroacetate                                                                       Sodium o-phenylphenolate                                  Subtilis                           95/5  500    9 × 10                                                      95/5  1000   7                                                                 90/10 500    8 × 10                                                      90/10 1000   0                                                                 80/20 500    6 × 10                                                      80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    23 × 10.sup.7                                               100/0 1000   9 × 10.sup.4                                                0/100 25     3 × 10.sup.7                                                0/100 50     15 × 10.sup.4                                               0/100 100    6 × 10.sup.3                                                0/100 200    9 × 10                   Bacillus                                                                               Potassium sorbate                                                                           Sodium o-phenylphenolate                                  subtilis                           95/5  500    15 × 10                                                     95/5  1000   2                                                                 90/10 500    12 × 10                                                     90/10 1000   1                                                                 80/20 500    6 × 10                                                      80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    7 × 10.sup.8                                                100/0 1000   5 × 10.sup.7                                                0/100 25     3 × 10.sup.7                                                0/100 50     15 × 10.sup.4                                               0/100 100    6 × 10.sup.3                                                0/100 200    9 × 10                   Bacillus                                                                               Sorbic acid  Sodium o-phenylphenolate                                  subtilis                           95/5  500    15 × 10                                                     95/5  1000   0                                                                 90/10 500    7 × 10                                                      90/10 1000   0                                                                 80/20 500    3 × 10                                                      80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    13 × 10.sup.6                                               100/0 1000   18 × 10.sup.4                                               0/100 25     3 × 10.sup.7                                                0/100 50     15 × 10.sup.4                                               0/100 100    6 × 10.sup.3                                                0/100 200    9 × 10                   Staphylococ-                                                                           Sodium dehydroacetate                                                                       2-(4-Thiazolyl)-1H-                                       cus aureus           benzimidazole 95/5  500    21 × 10                                                     95/5  1000   6 × 10                                                      90/10 500    20 × 10                                                     90/10 1000   9                                                                 80/20 500    19 × 10                                                     80/20 1000   8                                                                 60/40 500    8 × 10                                                      60/40 1000   5                                                                 100/0 500    19 × 10.sup.5                                               100/0 1000   18 × 10.sup.3                                               0/100 25     4 × 10.sup.9                                                0/100 50     4 × 10.sup.8                                                0/100 100    10 × 10.sup.6                                               0/100 200    5 × 10.sup.4             Staphylococ-                                                                           Potassium sorbate                                                                           2-(4-Thiazolyl)-1H-                                       cus aureus           benzimidazole 95/5  500    25 × 10                                                     95/5  1000   8 × 10                                                      90/10 500    24 × 10                                                     90/10 1000   15                                                                80/20 500    31 × 10                                                     80/20 1000   15                                                                60/40 500    29 × 10                                                     60/40 1000   10                                                                100/0 500    25 × 10.sup.7                                               100/0 1000   9 × 10.sup.5                                                0/100 25     4 × 10.sup.9                                                0/100 50     4 × 10.sup.8                                                0/100 100    10 × 10.sup.6                                               0/100 200    5 × 10.sup.4             Staphylococ-                                                                           Sorbic acid  2-(4-Thiazolyl)-1H-                                       cus aureus           benzimidazole 95/5  500    30 × 10.sup.2                                               95/5  1000   15 × 10                                                     90/10 500    41 × 10                                                     90/10 1000   35                                                                80/20 500    17 × 10                                                     80/20 1000   10                                                                60/40 500    6 × 10                                                      60/40 1000   5                                                                 100/0 500    21 × 10.sup.6                                               100/0 1000   5 × 10.sup.3                                                0/100 25     4 × 10.sup.9                                                0/100 50     4 × 10.sup.8                                                0/100 100    10 × 10.sup.6                                               0/100 200    5 × 10.sup.4             Staphylococ-                                                                           Sodium dehydroacetate                                                                       Methyl 1-(butylcarba-                                     cus aureus           moyl)-2-benzimidazole-                                                         carbamate     95/5  500    23 × 10                                                     95/5  1000   5                                                                 90/10 500    21 × 10                                                     90/10 1000   0                                                                 80/20 500    20 × 10                                                     80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    19 × 10.sup.5                                               100/0 1000   18 × 10.sup.3                                               0/100 25     7 × 10.sup.6                                                0/100 50     9 × 10.sup.4                                                0/100 100    12 × 10.sup.2                                               0/100 200    5 × 10                   Staphylococ-                                                                           Potassium sorbate                                                                           Methyl 1-(butylcarba-                                     cus aureus           moyl)-2-benzimidazole-                                                         carbamate     95/5  500    32 × 10                                                     95/5  1000   10 × 10                                                     90/10 500    19 × 10                                                     90/10 1000   0                                                                 80/20 500    28 × 10                                                     80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    25 × 10.sup.7                                               100/0 1000   9 × 10.sup.5                                                0/100 25     7 × 10.sup.6                                                0/100 50     9 × 10.sup.4                                                0/100 100    12 × 10.sup.2                                               0/100 200    5 × 10                   Staphylococ-                                                                           Dehydroacetate                                                                              Methyl 1-(butylcarba-                                      cus aureus          moyl)-2-benzimidazole-                                                         carbamate     95/5  500    30 × 10                                                     90/5  1000   9 × 10                                                      90/10 500    15 × 10                                                     90/10 1000   0                                                                 80/20 500    15 × 10                                                     80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    22 × 10.sup.5                                               100/0 1000   6 × 10.sup.3                                                0/100 25     7 × 10.sup.6                                                0/100 50     9 × 10.sup.4                                                0/100 100    12 × 10.sup.2                                               0/100 200    5 × 10                   Escherichia                                                                            Sodium dehydroacetate                                                                       Tetrachloroisophthalo-                                    coli                 nitrile       95/5  500    9                                                                 95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    7 × 10.sup.8                                                100/0 1000   9 × 10.sup.7                                                0/100 25     2 × 10.sup.5                                                0/100 50     9 × 10.sup.4                                                0/100 100    7 × 10.sup.2                                                0/100 200    3 × 10                   Escherichia                                                                            Potassium sorbate                                                                           Tetrachloroisophthalo-                                    coli                 nitrile       95/5  500    25                                                                95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    6 × 10.sup.9                                                100/0 1000   12 × 10.sup.7                                               0/100 25     2 × 10.sup.5                                                0/100 50     9 × 10.sup.4                                                0/100 100    7 × 10.sup.2                                                0/100 200    3 × 10                   Escherichi                                                                             Dehydroacetic acid                                                                          Tetrachloroisophthalo-                                    coli                 nitrile       95/5  500    15                                                                95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    13 × 10.sup.8                                               100/0 1000   31 × 10.sup.6                                               0/100 25     2 × 10.sup.5                                                0/100 50     9 × 10.sup.4                                                0/100 100    7 × 10.sup.2                                                0/100 200    3 × 10                   Pseudomonas                                                                            Sodium dehydroacetate                                                                       8-Hydroxyquinoline                                        aeruginosa           sulfate       95/5  500    9 × 10                                                      95/5  1000   0                                                                 90/10 500    5 × 10                                                      90/10 1000   0                                                                 80/20 500    8 × 10                                                      80/20 1000   0                                                                 60/40 500    4 × 10                                                      60/40 1000   0                                                                 100/0 500    15 × 10.sup.8                                               100/0 1000   2 × 10.sup.7                                                0/100 25     22 × 10.sup.6                                               0/100 50     21 × 10.sup.4                                               0/100 100    15 × 10.sup.2                                               0/100 200    4 × 10                   Pseudomonas                                                                            Potassium sorbate                                                                           8-Hydroxyquinoline                                        aeruginosa           sulfate       95/5  500    18 × 10                                                     95/5  1000   4                                                                 90/10 500    16 × 10                                                     90/10 1000   0                                                                 80/20 500    17 × 10                                                     80/20 1000   0                                                                 60/40 500    16 × 10                                                     60/40 1000   0                                                                 100/0 500    15 × 10.sup.10                                              100/0 1000   7 × 10.sup.8                                                0/100 25     22 × 10.sup.6                                               0/100 50     21 × 10.sup.4                                               0/100 100    15 × 10.sup.2                                               0/100 200    4 × 10                   Pseudomonas                                                                            Sorbic acid  8-Hydroxyquinoline                                        aeruginosa           sulfate       95/5  500    19 × 10                                                     95/5  1000   10                                                                90/10 500    21 × 10                                                     90/10 1000   8                                                                 80/20 500    17 × 10                                                     80/20 1000   0                                                                 60/40 500    14 × 10                                                     60/40 1000   0                                                                 100/0 500    9 × 10.sup.9                                                100/0 1000   8 × 10.sup.7                                                0/100 25     22 × 10.sup.6                                               0/100 50     21 × 10.sup.4                                               0/100 100    15 × 10.sup.2                                               0/100 200    4 × 10                   Pseudomonas                                                                            Sodium dehydroacetate                                                                       p-Chloro-m-xylenol                                        aeruginosa                         95/5  500    15 × 10                                                     95/5  1000   0                                                                 90/10 500    13 × 10                                                     90/10 1000   0                                                                 80/20 500    12 × 10                                                     80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    15 × 10.sup.8                                               100/0 1000   2 × 10.sup.7                                                0/100 25     8 × 10.sup.9                                                0/100 50     15 × 10.sup.6                                               0/100 100    18 × 10.sup.4                                               0/100 200    13 × 10.sup.2            Pseudomonas                                                                            Potassium sorbate                                                                           p-Chloro-m-xylenol                                        aeruginosa                         95/5  500    20 × 10                                                     95/5  1000   7                                                                 90/10 500    17 × 10                                                     90/10 1000   5                                                                 80/20 500    15 × 10                                                     80/20 1000   5                                                                 60/40 500    3 × 10                                                      60/40 1000   0                                                                 100/0 500    15 × 10.sup.10                                              100/0 1000   7 × 10.sup.8                                                0/100 25     8 × 10.sup.9                                                0/100 50     15 × 10.sup.6                                               0/100 100    18 × 10.sup.4                                               0/100 200    13 ×  10.sup.2           Pseudomonas                                                                            Sorbic acid  p-Chloro-m-xylenol                                        aeruginosa                         95/5  500    18 × 10                                                     95/5  1000   5                                                                 90/10 500    10 × 10                                                     90/10 1000   0                                                                 80/20 500    9 × 10                                                      80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    9 × 10.sup.9                                                100/0 1000   8 × 10.sup.7                                                0/100 25     8 × 10.sup.9                                                0/100 50     15 × 10.sup.6                                               0/100 100    18 × 10.sup.4                                               0/100 200    13 × 10.sup.2            __________________________________________________________________________

EXAMPLE 2

A 5% aqueous solution of starch was prepared and sterilized, and 100 ml. portions thereof were poured into 200 ml. bottles. After adding a prescribed amount of an antibacterial, antifungal composition consisting of the components (A) and (B) as shown in Table 2 to each bottle and thoroughly agitating, 1 ml. (number of fungi: 5×10⁶ fungi/ml.) of an aqueous suspension of fungi as shown in Table 2 was added to each bottle and was agitated again. The thus prepared aqueous solution contained 5×10⁴ fungi per gram. The bottles were then sealed and allowed to stand at 30° C. for a week. The state of the growth of fungi was observed by measuring the number of fungi in 1 g. of the aqueous solution.

The results are shown in Table 2.

                                      TABLE 2                                      __________________________________________________________________________                                              Amount of                                     Antibacterial, antifungal composition                                                                           composition                                                                           Number of                                                         (A)/(B)                                                                              added  fungi                          Fungi   Component (A)                                                                               Component (B) by weight                                                                            (p.p.m.)                                                                              (fungi/g.)                     __________________________________________________________________________     Trichoderma                                                                            Sodium dehydroacetate                                                                       N-(fluorodichloro-                                        viride               methylthio)phthalimide                                                                       95/5  100    4 × 10                                                      95/5  500    0                                                                 90/10 100    2 × 10                                                      90/10 500    0                                                                 80/20 100    8                                                                 80/20 500    0                                                                 60/40 100    0                                                                 100/0 100    29 × 10.sup.8                                               100/0 500    34 × 10.sup.5                                               0/100 5      7 × 10.sup.7                                                0/100 25     16 × 10.sup.6                                               0/100 50     33 × 10.sup.4                                               0/100 100    5 × 10.sup.2             Trichoderma                                                                            Potassium sorbate                                                                           N-(fluorodichloro-                                        viride               methylthio)phthalimide                                                                       95/5  100    8 × 10                                                      95/5  500    0                                                                 90/10 100    5 × 10                                                      90/10 500    0                                                                 80/20 100    7                                                                 80/20                                                                          60/40 100    0                                                                 100/0 100    27 × 10.sup.10                                              100/0 500    9 × 10.sup.8                                                0/100 5      7 × 10.sup.7                                                0/100 25     16 × 10.sup.6                                               0/100 50     33 × 10.sup.4                                               0/100 100    5 × 10.sup.2             Trichoderma                                                                            Dehydroacetic acid                                                                          N-(fluorodichloro-                                        viride               methylthio)phthalimide                                                                       95/5  100    3 × 10                                                      95/5  500    0                                                                 90/10 100    0                                                                 80/20 100    0                                                                 60/40 100    0                                                                 100/0 100    25 × 10.sup.8                                               100/0 500    30 × 10.sup.5                                               0/100 5      7 × 10.sup.7                                                0/100 25     16 × 10.sup.6                                               0/100 50     33 × 10.sup.4                                               0/100 100    5 × 10.sup.2             Cladosporium                                                                           Sodium dehydroacetate                                                                       Sodium o-phenylphenolate                                  resinae                            95/5  500    8 × 10                                                      95/5  1000   5                                                                 90/10 500    5                                                                 90/10 1000   0                                                                 80/20 500    5                                                                 80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    31 × 10.sup.6                                               100/0 1000   28 × 10.sup.3                                               0/100 25     8 × 10.sup.10                                               0/100 50     18 × 10.sup.8                                               0/100 100    34 × 10.sup.6                                               0/100 200    5 × 10                   Cladosporium                                                                           Potassium sorbate                                                                           Sodium o-phenylphenolate                                  resinae                            95/5  500    15 × 10                                                     95/5  1000   3                                                                 90/10 500    10 × 10                                                     90/10 1000   0                                                                 80/20 500    9                                                                 80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    13 × 10.sup.6                                               100/0 1000   25 × 10.sup.3                                               0/100 25     8 × 10.sup.10                                               0/100 50     18 × 10.sup.8                                               0/100 100    34 × 10.sup.6                                               0/100 200    5 × 10                   Cladosporium                                                                           Dehydroacetic acid                                                                          Sodium o-phenylphenolate                                  resinae                            95/5  500    7 × 10                                                      95/5  1000   0                                                                 90/10 500    4                                                                 90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    10 × 10.sup.5                                               100/0 1000   9 × 10.sup.3                                                0/100 25     8 × 10.sup.10                                               0/100 50     18 × 10.sup.8                                               0/100 100    34 × 10.sup.6                                               0/100 200    5 × 10                   Aspergillus                                                                            Sodium dehydroacetate                                                                       2-(4-Thiazolyl)-1H-                                       niger                benzimidazole 95/5  500    7 × 10                                                      95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    18 × 10.sup.10                                              100/0 1000   30 × 10.sup.4                                               0/100 25     37 × 10.sup.8                                               0/100 50     18 × 10.sup.5                                               0/100 100    11 × 10.sup.3                                               0/100 200    4 × 10                   Aspergillus                                                                            Potassium sorbate                                                                           2-(4-Thiazolyl)-1H-                                       niger                benzimidazole 95/5  500    21 × 10                                                     95/5  1000   3                                                                 90/10 500    3 × 10                                                      90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    7 × 10.sup.10                                               100/0 1000   37 × 10.sup.8                                               0/100 25     37 × 10.sup.8                                               0/100 50     18 × 10.sup.5                                               0/100 100    11 × 10.sup.3                                               0/100 200    4 × 10                   Aspergillus                                                                            Dehydroacetic acid                                                                          2-(4-Thiazolyl)-1H-                                       niger                benzimidazole 95/5  500    5 × 10                                                      95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    17 × 10.sup.10                                benzimidazole 100/0 1000   25 × 10.sup.4                                               0/100 25     37 × 10.sup.8                                               0/100 50     18 × 10.sup.5                                               0/100 100    11 × 10.sup.3                                               0/100 200    4 × 10                   Penicillium                                                                            Sodium dehydroacetate                                                                       Methyl 1-(butylcarba-                                     citrinum             moyl)-2-benzimidazole-                                                                       95/5  500    23 × 10                                       carbamate     95/5  1000   8                                                                 90/10 500    2 × 10                                                      90/10 1000   0                                                                 80/20 5000   5                                                                 80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    17 × 10.sup.5                                               100/0 1000   35 × 10.sup.4                                               0/100 25     13 × 10.sup.8                                               0/100 50     19 × 10.sup.6                                               0/100 100    9 × 10.sup.3                                                0/100 200    3 × 10                   Penicillium                                                                            Potassium sorbate                                                                           Methyl 1-(butylcarba-                                     citrinum             moyl)-2-benzimidazole-                                                                       95/5  500    19 × 10                                       carbamate     95/5  1000   9                                                                 90/10 500    10 × 10                                                     90/10 1000   1                                                                 80/20 500    7                                                                 80/20 1000   0                                                                 60/40 500    0                                                                 100/0 500    4 ×  10.sup.9                                               100/0 1000   12 × 10.sup.7                                               0/100 25     13 × 10.sup.8                                               0/100 50     19 × 10.sup.6                                               0/100 100    9 × 10.sup.3                                                0/100 200    3 × 10                   Penicillium                                                                            Sorbic acid  Methyl 1-(butylcarba-                                     citrinum             moyl)-2-benzimidazole-                                                                       95/5  500    8 × 10                                        carbamate     95/5  1000   5                                                                 90/10 500    5 × 10                                                      90/10 1000   2                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    7 × 10.sup.7                                                100/0 1000   40 × 10.sup.5                                               0/100 25     13 × 10.sup.8                                               0/100 50     19 × 10.sup.6                                               0/100 100    9 × 10.sup.3                                                0/100 200    3 × 10                   Aspergillus                                                                            Sodium dehydroacetate                                                                       Tetrachloroisophthalo-                                    niger                nitrile       95/5  100    2                                                                 95/5  500    0                                                                 90/10 100    0                                                                 80/20 100    0                                                                 60/40 100    0                                                                 100/0 100    25 × 10.sup.10                                              100/0 500    18 × 10.sup.7                                               0/100 5      7 × 10.sup.4                                                0/100 25     8 × 10.sup.3                                                0/100 50     3 × 10                   Aspergillus                                                                            Potassium sorbate                                                                           Tetrachloroisophthalo-                                    niger                nitrile       95/5  100    13 × 10                                                     95/5  500    0                                                                 90/10 100    0                                                                 80/20 100    0                                                                 60/40 100    0                                                                 100/0 100    33 × 10.sup.11                                              100/0 500    7 × 10.sup.10                                               0/100 5      7 × 10.sup.4                                                0/100 25     8 × 10.sup.3                                                0/100 50     3 × 10                   Aspergillus                                                                            Sorbic acid  Tetrachloroisophthalo-                                    niger                nitrile       95/5  100    10 × 10                                                     95/5  500    0                                                                 90/10 100    0                                                                 80/20 100    0                                                                 60/40 100    0                                                                 100/0 100    32 × 10.sup.10                                              100/0 500    5 × 10.sup.9                                                0/100 5      7 × 10.sup.4                                                0/100 25     8 × 10.sup.3                                                0/100 50     3 × 10                   Aspergillus                                                                            Sodium dehydroacetate                                                                       8-Hydroxyquinoline                                        niger                sulfate       95/5  500    3                                                                 95/5  1000   0                                                                 90/10 500    2                                                                 90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    18 × 10.sup.7                                               100/0 1000   30 × 10.sup.4                                               0/100 25     10 × 10.sup.6                                               0/100 50     7 × 10.sup.3                                                0/100 100    6 × 10.sup.2                                                0/100 200    6 × 10                   Aspergillus                                                                            Potassium sorbate                                                                           8-Hydroxyquinoline                                        niger                sulfate       95/5  500    13 × 10                                                     95/5  1000   0                                                                 90/10 500    8                                                                 90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    7 × 10.sup.10                                               100/0 1000   37 × 10.sup.8                                               0/100 25     10 × 10.sup.6                                               0/100 50     7 × 10.sup.3                                                0/100 100    6 × 10.sup.2                                                0/100 200    6 × 10                   Aspergillus                                                                            Dehydroacetic acid                                                                          8-Hydroxyquinoline                                        niger                sulfate       95/5  500    2                                                                 95/5  1000   0                                                                 90/10 500    2                                                                 90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    10 × 10.sup.7                                               100/0 1000   25 × 10.sup.4                                               0/100 25     10 × 10.sup.6                                               0/100 50     7 × 10.sup.3                                                0/100 100    6 × 10.sup.2                                                0/100 200    6 × 10                   Aspergillus                                                                            Sodium dehydroacetate                                                                       p-Chloro-m-xylenol                                        niger                              95/5  500    10 × 10                                                     95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    18 × 10.sup.7                                               100/0 1000   30 × 10.sup.4                                               0/100 25     14 × 10.sup.9                                               0/100 50     16 × 10.sup.6                                               0/100 100    12 × 10.sup.4                                               0/100 200    5 × 10                   Aspergillus                                                                            Potassium sorbate                                                                           p-Chloro-m-xylenol                                        niger                              95/5  500    15 × 10                                                     95/5  1000   0                                                                 90/10 500    5 × 10                                                      90/10 1000   0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    7 × 10.sup.10                                               100/0 1000   37 × 10.sup.8                                               0/100 25     14 × 10.sup.9                                               0/100 50     16 × 10.sup.6                                               0/100 100    12 × 10.sup.4                                               0/100 200    5 × 10                   Aspergillus                                                                            Dehydroacetic acid                                                                          p-Chloro-m-xylenol                                        niger                              95/5  500    6 × 10                                                      95/5  1000   0                                                                 90/10 500    0                                                                 80/20 500    0                                                                 60/40 500    0                                                                 100/0 500    10 × 10.sup.7                                               100/0 1000   25 × 10.sup.4                                               0/100 25     14 × 10.sup.9                                               0/100 50     16 × 10.sup.6                                               0/100 100    12 × 10.sup.4                                               0/100 200    5 × 10                   __________________________________________________________________________

EXAMPLE 3

A 2% of aqueous solution of carboxymethyl cellulose was prepared and adjusted to pH 7. After adding an antibacterial, antifungal composition consisting of the components (A) and (B) to the solution in a concentration as shown in Table 3, a slight amount of a putrid carboxymethyl cellulose was added to the solution. The solution was stored in an air-conditioned room at 37° C. and the putrefaction of the solution was obserbed with the lapse of time.

The results are shown in Table 3, in which symbols are as follows:

-: No putrefaction

+: Putrefaction

                                      TABLE 3                                      __________________________________________________________________________     Antibacterial, antifungal composition                                                      Concent-          Concent-                                                                            Time elapsed                                            ration            ration                                                                              After                                                                              After                                                                               After                              Component (A)                                                                              (p.p.m.)                                                                            Component (B)                                                                               (p.p.m.)                                                                            1 week                                                                             2 weeks                                                                             3 weeks                            __________________________________________________________________________     Sodium dehydroacetate                                                                      500  Sodium o-phenylphenolate                                                                    10   -   -    -                                  Potassium sorbate                                                                          500  Sodium o-phenylphenolate                                                                    50   -   -    -                                  --          0    Sodium o-phenylphenolate                                                                    100  -   +    +                                  Sodium dehydroacetate                                                                      2000 --           0    -   -    +                                  Potassium sorbate                                                                          2000 --           0    -   +    +                                  --          0    --           0    +   +    +                                  __________________________________________________________________________

EXAMPLE 4

An antibacterial, antifungal composition was added to a 6% aqueous solution of glue in a concentration as shown in Table 4. The solution was stored in an air-conditioned room at 50° C. and the decrease of the viscosity due to putrefaction was observed with the lapse of time.

The results are shown in Table 4, in which symbols are as follows:

-: No decrease of viscosity

+: Decrease of viscosity

                                      TABLE 4                                      __________________________________________________________________________     Antibacterial, antifungal composition                                                                             Time elapsed                                            Concent-          Concent-                                                     ration            ration                                                                              After                                                                              After                                                                               After                              Component (A)                                                                              (p.p.m.)                                                                            Component (B)                                                                               (p.p.m.)                                                                            1 week                                                                             2 weeks                                                                             3 weeks                            __________________________________________________________________________     Sodium dehydroacetate                                                                      1000 Sodium o-phenylphenolate                                                                    50   -   -    -                                  Potassium sorbate                                                                          2000 Sodium o-phenylphenolate                                                                    50   -   -    -                                  --          0    Sodium o-pehnylphenolate                                                                    200  +   +    +                                  Sodium dehydroacetate                                                                      5000 --            0   -   -    +                                  Potassium sorbate                                                                          5000 --            0   -   -    +                                  --          0    --            0   +   +    +                                  __________________________________________________________________________

EXAMPLE 5

An antibacterial, antifungal composition was added to an ethylene-vinyl acetate copolymer emulsion containing polyvinyl alcohol as an emulsifier in a concentration as shown in Table 5. A slight amount of a putrid emulsion was added to the emulsion and the number of cells was immediately measured. The emulsion was then stored in an air-conditioned room at 30° C., and after 3 weeks, the number of cells in the emulsion was measured again to determine the preservative and fungicidal effects.

The results are shown in Table 5.

                                      TABLE 5                                      __________________________________________________________________________     Antibacterial, antifungal composition                                                                    Number of cells (cell/g.)                                    Concent-     Concent-                                                          ration       ration                                                                              Before storage After 3 weeks                         Component (A)                                                                          (p.p.m.)                                                                            Component (B)                                                                          (p.p.m.)                                                                            Fungi                                                                               Yeast                                                                               Bacteria                                                                            Fungi                                                                               Yeast                                                                               Bacteria                    __________________________________________________________________________     Potassium de-                                                                          3000 Sodium o-phe-                                                                          100  51 × 10.sup.6                                                                 15 × 10.sup.6                                                                 7 × 10.sup.3                                                                  <10.sup.2                                                                           <10.sup.2                                                                           2 × 10.sup.2          hydroacetate nylphenolate                                                      Potassium                                                                              4000 Sodium o-phe-                                                                          200  35 × 10.sup.6                                                                 19 × 10.sup.6                                                                 5 × 10.sup.3                                                                  <10.sup.2                                                                           <10.sup.2                                                                           4 × 10.sup.2          sorbate      nylphenolate                                                      Potassium                                                                              0    Sodium o-phe-                                                                          1000 25 × 10.sup.6                                                                 19 × 10.sup.6                                                                 9 × 10.sup.3                                                                  31 × 10.sup.5                                                                 22 × 10.sup.5                                                                 9 × 10.sup.3          sorbate      nylphenolate                                                      Sodium de-                                                                             5000 Sodium o-phe-                                                                          0    30 × 10.sup.6                                                                 26 × 10.sup.6                                                                 6 × 10.sup.3                                                                  72 × 10.sup.4                                                                 18 × 10.sup.4                                                                 6 × 10.sup.3          hydroacetate nylphenolate                                                      Potassium                                                                              5000 Sodium o-phe-                                                                          0    17 × 10.sup.6                                                                 24 × 10.sup.6                                                                 6 × 10.sup.3                                                                  10 × 10.sup.6                                                                 29 × 10.sup.5                                                                 5 × 10.sup.3          sorbate      nylphenolate                                                      Potassium                                                                              0    Sodium o-phe-                                                                          0    51 × 10.sup.6                                                                 18 × 10.sup.6                                                                 8 × 10.sup.3                                                                  23 × 10.sup.7                                                                 25 × 10.sup.6                                                                 8 × 10.sup.3          sorbate      nylphenolate                                                      __________________________________________________________________________

EXAMPLE 6

A 10% aqueous solution of a polyvinyl alcohol sizing agent was prepared and divided into three portions. To the first portion was added no medicine, to the second portion was added 2,000 p.p.m. of sodium dehydroacetate, and to the third portion were added 1,000 p.p.m. of sodium dehydroacetate and 100 p.p.m. of p-chloro-m-xylenol. Epicoccum sp. was inoculated to each of the three portions, and they were placed in an incubator at 30° C. and allowed to stand for 14 days.

In the first and second portions, development of fungi was observed after 3 and 5 days, respectively, but in the third position no development of fungi was observed.

The above procedure was repeated except that, as the component (B), 2-(4-thiazolyl)-1H-benzimidazole, 8-hydroxyquinoline sulfate, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, tetrachloroisophthalonitrile or N-(fluorodichloromethylthio)phthalimide was employed instead of p-chloro-m-xylenol. The same results as above were obtained with respect to all the above compounds.

EXAMPLE 7

The procedures of Example 6 were repeated except that potassium sorbate was employed instead of sodium dehydroacetate.

With respect to all tests using six components (B) in Example 6, in the first and second portions development of fungi was observed after 4 and 6 days, respectively, but in the third portion no development of fungi was observed.

EXAMPLE 8

An antibacterial, antifungal composition was prepared by admixing 95 g. of sodium dehydroacetate as the component (A) and 5 g. of the component (B) shown in Table 6. The composition was added to a 18% solution of a crotonic acid-vinyl acetate copolymer in a concentration of 2,500 p.p.m., 5,000 p.p.m. or 7,500 p.p.m. to give three kinds of the coating solutions.

Each solution was sprayed onto two sides of a fancy mat (10×10 cm.) in an amount of 2 g. on each side, and was then dried at 140° C. for 2 minutes.

The coated fancy mats were allowed to stand under a saturated humidity at 25° C., and the state of the growth of fungi was observed with the lapse of time.

The results are shown in Table 6, in which symbols are as follows:

-: No growth

±: A little growth

+: Growth (The more the number of the symbol +, the larger the growth.)

                                      TABLE 6                                      __________________________________________________________________________            Concentration                                                                  of composition    Days elapsed                                          Component (B)                                                                         (p.p.m.)          5  6  7  8   10   12    14                            __________________________________________________________________________     p-Chloro-m-xylenol                                                                              0       -  -  +  ++  +++  +++++ +++++                                          2500    -  -  ±                                                                              +   +++  +++   ++++                                           5000    -  -  -  ±                                                                               +    ++    +++                                            7500    -  -  -  -   -    -     -                             2-(4-Thiazolyl)-1H-benzimidazole                                                                0       -  +  ++ +++ ++++ +++++ +++++                                          2500    -  -  +  +   +++  +++   ++++                                           5000    -  -  -  ±                                                                               +    ++    +++                                            7500    -  -  -  -   -    -     -                             8-Hydroxyquinoline sulfate                                                                      0       -  +  ++ +++ ++++ +++++ +++++                                          2500    -  -  +  +   +++  +++   ++++                                           5000    -  -  -  ±                                                                               +    ++    +++                                            7500    -  -  -  -   -    -     -                             Methyl 1-(butylcarbamoyl)-2-benz-                                              imidazolecarbamate                                                                              0       -  +  ++ +++ ++++ +++++ +++++                                          2500    -  -  +  +   +++  +++   ++++                                           5000    -  -  -  ±                                                                               +    ++    +++                                            7500    -  -  -  -   -    -     -                             Tetrachloroisophthalonitrile                                                                    0       -  +  ++ +++ ++++ +++++ +++++                                          2500    -  -  ±                                                                              +   +++  +++   ++++                                           5000    -  -  -  -   ± +     +                                              7500    -  -  -  -   -    -     -                             N-(fluorodichloromethylthio)-                                                  phthalimide      0       -  +  ++ +++ ++++ +++++ +++++                                          2500    -  ±                                                                              +  +   +++  +++   ++++                                           5000    -  -  -  ±                                                                               +    ++    +++                                            7500    -  -  -  -   -    -     -                             __________________________________________________________________________

EXAMPLE 9

A sizing solution containing 5% of wheat starch and a sizing solution containing 5% a casein were prepared, and thereto was added an antibacterial or antifungal agent as shown in Table 7. After adding a suspension of fungi consisting of Aspergillus niger, Penicillium citrinum, Cladosporium herbaum and Chaetomium globosum to each of the sizing solutions, the sizing solutions were placed in an incubator at 28° C. and the state of the growth of fungi was observed with the lapse of time.

The results are shown in Table 7, in which symbols are as follows:

-: No growth

±: A little growth

+: Growth (The more the number of the symbol +, the larger the growth.)

                                      TABLE 7                                      __________________________________________________________________________     Sizing                       Incubation days                                   solution                                                                              Antibacterial, antifungal agent                                                                      0  4  7   14   21   28                            __________________________________________________________________________     Wheat starch                                                                             None               -    +                                                                               +++ ++++ ++++ ++++                          Casein    None               -    -                                                                               ++  +++  ++++ ++++                          Wheat Starch                                                                          Sodium dehydroacetate (500 p.p.m.)                                                                   -    -                                                                               ±                                                                               ++   +++  +++                           Casein Sodium dehydroacetate (500 p.p.m.)                                                                   -    -                                                                               -   +    ++   +++                           Wheat starch                                                                          Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    p-Chloro-m-xylenol (25 p.p.m.)                                          Casein Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    p-Chloro-m-xylenol (25 p.p.m.)                                          Wheat starch                                                                          Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    2-(4-Thiazolyl)-1H-benzimidazole (25 p.p.m.)                            Casein Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    2-(4-Thiazoly-1H-benzimidazol                                           25 p.p.m.)                                                                     Wheat starch                                                                          Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    8-Hydroxyquinoline sulfate (25 p.p.m.)                                  Casein Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    8-Hydroxyquinoline sulfate (25 p.p.m.)                                  Wheat starch                                                                          Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    Methyl 1-(butylcarbamoyl)-2-benzimidazole                                      carbamate (25 p.p.m.)                                                   Casein Sodium dehydroacetate (475 p.p.m. and                                                                -    -                                                                               -   -    -    -                                    Methyl 1-(butylcarbamoyl)-                                                     2-benzimidazolecarbamate (25 p.p.m.)                                    Wheat starch                                                                          Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    Tetrachloroisophthalonitrile 25 p.p.m. and                              Sodium dehydroacetate (475 p.p.m.) and                                         Casein Sodium dehydroacetate (475 p.p.m.) and                                  -      -                     -    -                                                                               -   -                                       Wheat Starch                                                                          Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    N-(fluorodichloromethylthio)phthalimide                                        (25 p.p.m.)                                                             Casein Sodium dehydroacetate (475 p.p.m.) and                                                               -    -                                                                               -   -    -    -                                    N-(fluorodichloromethylthio)phthalamide                                        (25 p.p.m.)                                                             __________________________________________________________________________ 

What we claim is:
 1. An antibacterial and antifungal composition comprising a mixture of:(A) at least one member selected from the group consisting of sorbic acid, and its alkali metal salts; and (B) 2-(4-thiazolyl)-1H-Benzimidazole, wherein the weight ratio of component (A) to component (B) is in the range of 95/5 to 60/40. 